Perfume manufacture



Sept. 23, 1941.

W. FREUDENBERG 2,256,772 PERF ME MANUFACTURE Filed Dec. 18, 1967 ETALs AND/ore OTHER FLowEra Pems EussmNMINEIzAL On. ore HYDIZOCREBON Coummme CYCLICTEIZPENE-LIKE COnPOUNDS Heating to 25"-50C.

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F'LLter Mechanical vol ume 80-90% alcohol (24 hours) to obta'm extract Ln alcohol Shaking of HLtmhe with On. Com-mums shakmg wnkh 2X volume 5 to obtain extract Ln. alco some Ex'rrencr z 'firealgment of oitbg hot mechanical 90% alcohol mam-10L PHASE CONTAINING EXTRACT Separation.

Separation.

QLcoHoL. PHASE Plzsszzvzra Dun-m PHTHALATE commmue ExTraec-r F'LLterinq Combined. Extracts MlNERAL On. Fora mausa oz BENZYL Bznzom'c oration. in. vacuo Evaip o solvent alcohol.

ETHEraEAL 0n. CONCENTRATES Patented Sept. 23, 1941 PERFUME MANUFACTURE Werner Freudenberg, Scarsdale, N. Y., assignor to Thomas Young Nurseries, Inc., Bound Brook, N. J a corporation of New Jersey Application December 18, 1937, Serial No. 180,659 I 19 Claims.

My invention relates to the manufacture of perfumes from plants, either growing'or dried, and for example it deals with the manufacture of perfumes, such as orchid perfume, from the petals or other flower parts of orchids, or other plants. 7

The extraction of certain of the ethereal oils from plants is in many cases exceedingly difficult, since the ethereal oils may quickly change their chemical composition and lose the desired odor. Moreover the processes now in use do not seem to enable certain of the more delicate perfumes to be extracted from flowers. For instance, the orchid perfume, which is highly desirable as a scent for toilet purposes and other uses, has, to my knowledge, never been successfully commercially obtained.

The orchid perfume is highly volatile, and the ethereal oils which give the odor are difficult to extract and difficult to maintain in their desired chemical state so that the original odor is preserved.

An object of my invention is to provide a process which will extract ethereal oils from plants and enable them to be made into perfumes.

Another object of my invention is to provide an enfluerage process which will enable the elusive ethereal oils to be extracted from flower parts of orchids and other plants.

A further object of my invention is to provide a defluerage step wherein the ethereal oils having been extracted from the flower parts may be brought into solution with a proper solvent for the ethereal oils, without dissolving the material used for the enfleurage. v

Yet another object of my invention is to provide novel preservers for ethereal oils.

My invention comprises the steps of subject ing plant parts, such as the flowerparts or petals of plants, to an enfleurage process wherein the ethereal oils which give the desired odor are caught in oil, which is in general a hydrocarbon; I have found that a liquid hydrocarbon which contains cyclic compounds of a terpene-like nature is the best type of compound to employ for this purpose. The oil is then subjected to a defluerage process in which the solvent removes the ethereal oils from the hydrocarbon oil. Preservatives are added to preserve the ethereal oils while the solvent is removed by distillation to ive an ethereal oil concentrate containing a preservative, or preservatives. This material can be employed as a perfume base.

Referring to the single figure of the drawing, I have shown a type of process which illustrates in general my method of conducting the manufacture of the perfume. It is to be understood that I can vary this process within the scope of the claims, and that the drawing is merely illustrative of a desirable method which I can employ.

The orchids or other flowers quickly, after being gathered, have their petals and other flower parts removed, and these are covered in a closed vessel with oil, such as Russian mineral oil, which contains cyclic compounds of terpene-like nature.

This stepof theproces's, which is the enfleurage step, may be continued at a temperature of about to C. until wilting of the flower parts is evident. This means that osmotic changes have occurred and the ethereal oils have passed from the flower parts into the oil. The step may take a number of days, and even weeks. I have found that normally this enfleurage step will take from two to fourweeks. After the enfleurage step, a filtering step may be employed to separate the flower parts from the Russian mineral oil or other hydrocarbons containing cyclic terpenes, but in many instances mere decantation is suflici-ent to separate the oil from the flower parts. I v

Next I subject the mineral oil to-a defieurage step in which the ethereal oils are extracted from the mineral oils by a suitable solvent. Ina'typical process I subject the mineral oil to a mechanical shaking with approximately twice the volume of the mineral oil of to per cent ethyl alcohol. Under certain circumstances I may employ other alcohols. The mechanical shaking may be continued for approximately twentyfour hours. The alcohol phase is'then separated from the oil and the residual oil is in my preferred process subjected to a second mechanical shaking with approximately twice its volume of 80 to 90 percent ethyl alcohol. The extract in the alcohol phase is separated from the oil and is combined with the first extract. The residual mineral oil from both of these defleurage steps can be used again for'treating fresh batches of flowers.

The combined alcohol extracts are filtered and a preserver is added. The preserver has the effect of preventing change in the chemical composition of the ethereal oils which gives the desired odor. I, in general, employ approximately one percent of diethyl phthalate or one percent of benzyl benzoate. Two preservatives may be combined if desired, in which case less quantity of each is used'so that the combined preservatives base.

, It is important in the defleurage step that the ethyl alcohol be diluted with water to 80 to 90 percent. This isdone for the purpose of making the alcohol immiscible with the oil. The dilution has furthermore the advantage of preventing the absorption by the alcohol of the bad smelling terpenes.

. It is to be understood that I 91mm be limited only by the showing of the prior art and the scope of the appended claims.v I e I claim: 7 7 '1. In a process of defleurage of a naphthenic mineral oil containing ethereal oils, the step of treating the naphthenic mineral oil with 80 to .90 per cent alcohol to extract the ethereal oils.

, 2. Aprocess; of defleurage of Russian mineral oils containing the etheral oils of orchids com- }prising treating the Russian mineral oil containing said ethereal oils with approximately twice its volume of; 80 to 90 percent ethyl alcohol for approximately twenty-four hours, while mechan- Iically agitating the mixture whereby the ethereal oils are extracted from the Russian mineral oil and pass into thealcohol; j 3. Aprocess for manufacturing orchid perfume comprising an enfleurage step in which the flower parts of the orchids are subjected-to a bath of a Russian mineral oil containing cyclic terpenelike compounds while maintaining a temperature of between 25 and 50". C. untilthe flower parts become wilted, then subjecting the hydrocarbon oil to adefleurage step comprising extracting the joil-byagitation with an 80, to 90% alcohol solu-' tion-,jtreating the extract witha preservative for evaporating the solvent to obtain an ethereal oil concentrate. 1

5; Inthe manufacture of a perfume, an enfleurage 'step' comprising subjecting the portions "of plants containing the desirable ethereal oil to a bath of a Russian mineral oil, then subjecting V the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with 80 to 90 per cent ethyl alcohol, thentreating the extract with a preservative for the ethereal oil contained in the solvent, and then evaporating r the solvent to obtain an ethereal oil concentrate.

6. .A process for manufacturing orchid perfume comprising an enfleurage step in which'the flower parts of the orchids are subjected to a bath of a fnaphthenic hydrocarbon oil while maintaining a temperature of between 25 and 50 C. until the 'jflo'wer parts become wilted, then subjecting the hydrocarbon oil to a defleurage step comprisin extracting the oil by agitation with 80 to 90 percent ethyl alcohol, treating the extract with a preservative for the ethereal oil contained in the solvent, and then evaporating the solvent to obparts of the orchids are subjected to a bath of.

, Russian mineral oil while maintaining a term perature of between 25 and 50 C. until the flower parts become wilted, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with approximately twice the volume of the mineral oil of 80 to 90 percent ethyl alcohol to extract the ethereal oils in themineral oil, maintaining such agitation for approximately twenty-four hours to obtain the extract, then separating the alcohol phaseirorn the oil and subjecting the residual oil tova second treatment by mechanically agitating the mineral oil with approximately twice its volume of BOto 90 percent ethyl alcohoL then combining'the filtered alcohol extracts and adding thereto a preserver comprising diethylphthalate and benzyl benzoate-and evaporating the mixture in vacuo leaving the ethereal. oil concentrates remaining with the preserver.

8. A process for obtaining ethereal oils from growing plants. comprising an enfleurage step wherein the portions of the plants containing the desirable ethereal oil i subjected to abath of a hydrocarbon oil containing naphthenic compounds, then subjecting the hydrocarbon oil. to

a defleurage step wherein the, ethereal oils are extracted by agitation withfan 80 to 90% ethyl alcohol solution, then adding to. the extract diethyl phthalate as a preservative of the ethe-.

, real oil, and then evaporatingthe solvent .to,

obtain an ethereal oil concentrate. I r

. 9.-In the manufacture of. a perfume, an n-. fleurage step comprising subjecting the. portions of plants containing the desirable ethereal oil to a bath of a Russian mineral oil, then subjecting the Russian mineral oil to a defleurage step com prising extracting the oil by agitation with-8.0 to 90 percent ethyl alcohol, then treating the extract with diethyl phthalate as a preservative oil to a defleurage step comprising extracting the oil by agitation with 80 to 90 percent ethyl alcohol, treating the extract with diethyl phthalate asa preservative for the ethereal oil contained in the solvent, and then evaporating thesolv'ent to obtain an ethereal oil concentrate.-

11. A process for manufacturing orchid perfume comprising an enfleurage step in which the flower'parts of the orchidsare subjected-to a bath of Russian mineral 'oil while maintaining a temperature of between 25 and 50C. until the flower parts become wilted, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with'approxito obtain the extract, then separating thealcjoe.

hol phase from the oil and subjecting the residual oil to a second treatment by mechanically agitating the mineral oil with approximately twice its volume of 80 to 90 percent ethyl alcohol, then combining the filtered. alcohol extracts and adding thereto diethyl phthalate as a preserver, and evaporating the mixture in vacuo leaving the ethereal oil concentrates remaining with the preserver.

12. A process for manufacturing orchid perfume comprising an enfleurage step in which the flower parts of the orchids are subjected to a bath of Russian mineral oil while maintaining a temperature of between 25 and 50 C. until the flower parts become wilted, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with approximately twice the volume of the mineral oil of 80 to 90 percent ethyl alcohol to extract the ethereal oils in the mineral oil, maintaining such agitation for approximately twenty-four hours to obtain the extract, then separating the alcohol phase from the oil and subjecting the residual oil to a second treatment by mechanically agitating the mineral oil with approximately twice its volume of 80 to 90 percent ethyl alcohol, then combining the filtered alcohol extracts and adding thereto one percent of diethyl phthalate as a preservative, and evaporating the mixture in vacuo leaving the ethereal oil concentrates remaining with the preserver.

13. In a process of defleurage of a naphthenic mineral oil containing ethereal oils, the step of treating the naphthenic mineral oil with an 80 to 90 percent solution of alcohol to extract the ethereal oils, adding to the extract diethyl phthalate as a preservative for the ethereal oils, and then evaporating the solvent to obtain an ethereal oil concentrate.

14. A process for obtaining ethereal oils from growing plants comprising an enfleurage step wherein the portions of the plants containing the desirable ethereal oil is subjected to a bath of a hydrocarbon oil containing naphthenic compounds, then subjecting the hydrocarbon oil to a defleurage step wherein the ethereal oils are extracted by agitation with an 80 to 90% ethyl alcohol solution, then adding to the extract benzyl benzoate as a preservative of the ethereal oil contained in the solvent, and then evaporating the solvent to obtain an ethereal oil concentrate.

15. In the manufacture of a perfume, an enfleurage step comprising subjecting the portions of plants containing the desirable ethereal oil to a bath of a Russian mineral oil, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with 89 to 90 percent ethyl alcohol, then treating the extract with benzyl benzoate as a preservative for the ethereal oil contained in the solvent, and then evaporating the solvent to obtain an ethereal oil concentrate.

16. A process for manufacturing orchid perfume comprising an enfleurage step in which the flower parts of the orchids are subjected to a bath of a hydrocarbon oil containing naphthenic compounds while maintaining a temperature of between 25 and 50 C. until the flower parts become wilted, then subjecting the hydrocarbon oil to a defieurage step comprising extracting the oil by agitation with to percent ethyl alcohol, treating the extract with benzyl benzoate as a preservative for the ethereal oil contained in the solvent, and then evaporating the solvent to obtain an ethereal oil concentrate.

17. A process for manufacturing orchid perfume comprising an enfleurage step in which the flower parts of the orchids are subjected to a bath of Russian mineral oil while maintaining a I temperature of between 25 and 50 C. until the flower parts become wilted, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with approximately twice the volume of the mineral oil of 80 to 90 percent ethyl alcohol to extract the ethereal oils in the mineral oil, maintaining such agitation for approximately twenty-four hours to obtain the extract, then separating the alcohol phase from the oil and subjecting the residual oil to a second treatment by mechanically agitating the mineral oil with approximately twice its volume of 80 to 90 percent ethyl alcohol, then combining the filtered alcohol extracts and adding thereto benzyl benzoate as a preserver, and evaporating the mixture in vacuo leaving the ethereal oil concentrates remaining with the preserver.

18. A process for manufacturing orchid per.- fume comprising an enfleurage step in which the flower parts of the orchids are subjected to a bath of Russian mineral oil while maintaining a temperature of between 25 and 50 C. until the flower parts become wilted, then subjecting the Russian mineral oil to a defleurage step comprising extracting the oil by agitation with approximately twice the volume of the mineral oil of 80 to 90 percent ethyl alcohol to extract the ethereal oils in the mineral oil, maintaining such agitation for approximately twenty-four hours to obtain the extract, then separating the alcohol phase from the oil and subjecting the residual oil to a second treatment by mechanically agitating the mineral oil with approximately twice its volume of 80 to 90 percent ethyl alcohol, then combining the filtered alcohol extracts and adding thereto one percent of benzyl benzcate as a preservative, and evaporating the mixture in vacuo leaving the ethereal oil concentrates remaining with the preserver.

19. In a process of defleurage of a naphthenic mineral oil containing ethereal oils, the step of treating the naphthenic mineral oil with an 80 to 90 percent solution of alcohol to extract the ethereal oils, adding to the extract benzyl benzoate as a preservative for the ethereal oils, and then evaporating the solvent to obtain an ethereal oil concentrate.

WERNER FREUDENBERG. 

